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| U | KF Shkëndija 79 | - | FK Pobeda | 0:1 (0:1) | ||
| R | FK Pobeda | - | KF Shkëndija 79 | 2:0 (1:0) | ||
| U: 07.11.2018 13:00 | R: 05.12.2018 13:00 | Winnaars: FK Pobeda | ||||
| U | Sileks Kratovo | - | FK Belasica | 0:2 (0:0) | ||
| R | FK Belasica | - | Sileks Kratovo | 2:0 (0:0) | ||
| U: 07.11.2018 13:00 | R: 05.12.2018 13:00 | Winnaars: FK Belasica | ||||
| U | FK AP Brera Strumica | - | KF Korabi | 3:1 (2:1) | ||
| R | KF Korabi | - | FK AP Brera Strumica | 1:6 (1:2) | ||
| U: 07.11.2018 13:00 | R: 05.12.2018 13:00 | Winnaars: FK AP Brera Strumica | ||||
| U | Makedonija GP | - | FK Rabotnički | 1:0 (0:0) | ||
| R | FK Rabotnički | - | Makedonija GP | 0:1 (0:0) | ||
| U: 07.11.2018 13:00 | R: 05.12.2018 13:00 | Winnaars: Makedonija GP | ||||
